


Caught Freckle Handed

by DRHPaints



Category: Conan O’Brien, Conan O’Brien RPF, Late Night Host RPF
Genre: Blow Jobs, Boss/Employee Relationship, Caught, Cunnilingus, Explicit Language, Explicit Sexual Content, F/M, Face-Fucking, Masturbation, Masturbation Interruptus, One Shot, Smut
Language: English
Status: Completed
Published: 2020-08-21
Updated: 2020-08-21
Packaged: 2021-03-07 01:21:26
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,355
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26028646
Author URL: https://archiveofourown.org/users/DRHPaints/pseuds/DRHPaints
Summary: Sophia,  an intern at the Conan show,  walks in on Conan masturbating in his office and offers to help him out.
Relationships: Conan O’Brien/Original Female Character
Kudos: 11





	Caught Freckle Handed

Holding a hand to the bag to check it was still warm, Sophia scurried down the hall. She’d only been working as an intern at the Conan show for a few months and this was her first time being sent out for his lunch. As the oldest of the students by a number of years, Sophia felt a constant need to prove herself, and even this small task seemed monumental as she wove past writers and crew members to get to Conan’s office.

Seeing Sona wasn’t at her desk, Sophia rushed past and burst into Conan’s office. “Mr. O’Brien, I have your Pad...Thai…” Sophia’s mouth fell open as the door swung shut behind her. Head tossed back against his office chair, handsome face strained, breathing hard, Conan was frantically pumping his cock in the half a moment before he realized he’d been interrupted and scrambled to cover himself.

“ _ Oh holy shit!”  _ Eyes wide, mouth agape, Conan’s pale skin went bright pink as he stared back at her. “I’m sorry, I...I thought I locked the door…” Conan swallowed hard, gaze shifting away from her, hands on the desk.

Sophia knew she should leave, should set the food on the desk, mutter something half-intelligible and avoid Conan in the hallways for a month. But she’d caught a peek at his hard cock in his freckled hand when she entered the room. It was massive. Long, thick, and beautiful. And even before getting the position on the show Sophia nursed a crush on Conan, found his weird antics and lanky form incredibly sexy, so when she first encountered him; tall, funny, and kinder than she could’ve imagined to a lowly intern, it only fed the fire.

“What, um…” Sophia cleared her throat. “What kind of video are you watching?”

Blinking rapidly, Conan looked at her as though she were speaking a different language. “Uh...what?”

“I’m just…” Crossing her arms across her body, Sophia shifted her weight to one side, tossing her crimson hair over her shoulder. “Curious. What you’re into.” Flicking her gaze up she met Conan’s crystalline blue eyes. He stared back at her silently for a moment and his tongue darted out over his thin lips, a habit Sophia wondered if he was aware of after all these years.

Conan looked to the computer screen, then to her, then back. Tilting it ever-so-slightly in her direction, Conan leaned back in his chair and covered the lower half of his face, holding out a hand in a  _ come see _ gesture.

Taking a deep breath, Sophia bit her lip and walked around the desk. Bending over, she saw a paused image of a pretty woman with a cock in her mouth, a video entitled,  _ All Deep Throating: Volume 5. _

Silent for a moment, Sophia turned away from him and Conan began to fidget, fearing an HR disaster. But she simply locked the office door before facing him again.

“I think we can manage that, sir.” Locking into her emerald eyes, Conan’s hand shook on the armrest as Sophia approached him, turning his chair slightly and kneeling. Sophia’s hands began to glide up his lithe thighs.

“Miss, um...Miss Dover, I don’t know if this is a good idea…” Conan stilled her wrists.

Smirking up at him, Sophia raised an eyebrow. “Oh, come on, sir.  _ Please? _ ” She tilted her head, biting her lower lip. “I want to suck your cock  _ so fucking badly. _ ” Rising, Sophia climbed up Conan’s long body. She could feel his shallow breathing as she lowered her lips to his ear. “ _ Don’t you want to see what my throat feels like? _ ” 

A shudder went through him and Conan emitted an audible gasp. Pulling back to look at his face, Conan’s eyes shifted from the door, to her eyes, to her curvaceous, red mouth before nodding.

“Yeah. Yeah, okay.”

Grinning, Sophia got to her knees once more and encouraged Conan to lift his hips so she could shimmy his black skinny jeans down to the floor. She wanted him as unencumbered as possible, and when she revealed his turgid cock,, Sophia gazed at it admiringly before encircling it with her fingers.

Stroking lightly, she first pressed a kiss to the head before flicking the slit with her tongue. Looking to Conan, he was watching her intently, hands gripping the chair and chest rising nervously.

Without warning Sophia extended her jaw and sank down, taking as much of him in as she could manage, and Conan inadvertently thrust forward, a large, freckled hand burying itself in her mass of auburn waves.

“ _ Oh fu-uh-uck! _ ” 

Hollowing her cheeks, Sophia sucked intensely, allowing drool to cascade down Conan’s shaft as she tugged him into her mouth with one hand, the other rolling his balls between her fingers.

“ _ Oh fuck! Your mouth! I...It’s… _ ” Conan’s hips rocked up into her face, eyes clenched shut as he guided her head. Focusing on the sensitive tip, Sophia pushed her tongue firmly on the underside, provoking broken whimpers from Conan who was losing all control, shoving her head down and starting to fuck Sophia’s face in earnest.

“ _ Yes! Suck me! You’re so good! Fuck, don’t stop! _ ” Conan whined, digging his heels into the carpet. Tasting his precum and feeling the throbbing threat of his orgasm, Sophia burrowed him in her mouth until she couldn’t take anymore, undulating her throat.

“ _ Oh fuck, I’m gonna cum! _ ” Tensing above her, Conan’s fingertips dug into her scalp and with a strangled cry his hips jerked forward against her face, the salty, rich taste of his cum trickling down the back of her throat as he relaxed back into the chair, chest heaving.

Rising, Sophia wiped her eyes and mouth while Conan pulled up his jeans and put himself away.

“Wow, that was...that was great, thanks.” He grinned sheepishly. 

Sophia smiled coyly, shrugging. “No problem, sir.” Standing, she brushed off her knees, combing her fingers through her hair and was preparing to leave when Conan caught her by the arm.

“Hey, where are you going?”

Furrowing her brow in confusion, Conan took her by the hips, rolling his chair back and pressing her against the desk. Staring at her as he unzipped Sophia’s jeans, there was only one word for Conan’s expression:  _ hungry. _

Peeling them off along with her panties, Conan encouraged her to lay back on the desk before spreading her legs wide. He spent a long time just studying her, looking between her thighs, running his lengthy fingers up the creamy insides and gently petting the lips of her sex before lifting a leg over each shoulder and parting her with two fingers. 

When Conan’s tongue started circling her clit, Sophia didn’t know what to do. The orange head working between her thighs was one she’d imagined many a time, and as her knuckles went white gripping the edge of the desk and she bit her lip fighting to stay silent, the real Conan was better than any fantasy.

Thin lips locking around her clit, Conan sucked her into his mouth and a shriek flew out of her throat. Sophia desperately hoped Sona wasn’t back from lunch yet as she ground her hips against Conan’s sharp jawline, dripping down his face. Hands fisting in his buoyant orange hair, Sophia couldn’t help but moan as her legs shook uncontrollably.

“ _ Conan! Yes! Fuck! FUCK! _ ” A large pale hand appeared and clamped over her mouth as Conan dug his sculpted chin forward, consuming her recklessly. Panting wet against his fingers, Sophia’s eyes rolled and her ankles jittered along his back as she came, nearly tearing the iconic hair from his scalp in the process. 

Emerging, Conan wiped his face and Sophia was left a limp pile of nothing on top of his desk for a few minutes until she could gather herself and pull her underwear and jeans back on.

“Well, that certainly wasn’t listed in the benefits when I applied for this position.” Sophia smiled, combing her hair back.

Conan chuckled. “No, no, I guess not.”

“Good thing.” Sophia polished one of his prominent cheekbones, raising an eyebrow. “Otherwise you’d have a line out the door.”

**Author's Note:**

> Thank you for taking the time to read! If you enjoyed this, please leave a comment or come say hi on tumblr at fandomtransmandom


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